My Journey

Hi, I’m Jessie May—

I’m grateful to meet you. If you landed here, you’re probably someone who feels deeply, dreams boldly, and knows there’s more to life than what meets the eye.

I’ve always been led by my curious heart—drawn to what’s real, raw, and alive. That rhythm has carried me across continents and through many chapters: from my roots in Montreal to my life in LA, through creative ventures in fashion to guiding healing spaces and coaching women through seasons of change.

I’ve built businesses, navigated heartbreak, burned out, rebuilt, and returned—again and again—to what matters most: connection, truth, and the courage to trust.

At the heart of it all is a deep devotion to the fire that lives in each one of us.

My work is an invitation—whether through Sunny Side Up, a session with a brave founder, activating a community experience or a guided audio journey—to come home to yourself.

To trust your voice.
To feel with flow instead of force.
To remember what the world taught you to forget: that your presence is your power. Your heart is your compass.

I believe we all know each other by heart. And when our hearts are held, and we feel seen, we remember who we are.

We come alive with the courage, creativity, and passion on purpose that we’re all made of.

If your path feels unclear, your light has been dimmed, or you feel disconnected - yet you know you’ve got so much to share and express —I want you to know that you’re not alone.

I’ve been there. And I’m here to walk beside, and love you strong you as you rise. And Roar. To root in your radiance. The hearbeat of your being. To come home to YOUR Signature Song.

Because your presence is your power. And your radiance is wildly contagious.

I see you brave one. Thank you for being here. For showing up and remembering. Reach out and let’s get that heart fuego rebooted.

With big warm love,
Jessie May
@jessiemaywolfe